Digital Business Checklist

Digital Business Strategy Checklist

The Definitive Starting Point for Your Digital Business Journey

Getting started with your technology strategy? Perhaps you’re kicking off a hunt for the next greatest solution to rocket your growth in to the future. Maybe it’s a simple as trying to get a handle on what you have today and how it can be utilized better to enable your operations.

Whatever the reason, there are a handful of important items that you should have in hand before you go out and evaluate options and make a decision on the path forward. There are a number of examples of technology projects gone bad. Does this story sound familiar?

You may have noticed common themes in these examples. In every instance, there was not enough time spent up front doing the heavy lifting, understanding how work is done, the objectives of a solution and what the technology will do to support the business.

Here are five things on your digital business strategy checklist that you must have in hand (and why they are important) before you start looking at your solution options. Spoiler alert – the most important one is the last one!

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Many a technology project has gone off the rails before they ever get any momentum due to a lack of clarity of what you’re trying to achieve. There are simply too many choices, too many sources of information in 2019. Having a clear set of objectives helps immediately to narrow these choices and focuses the decision-making process. When I say “Documented Objectives”, I mean write them down – not just think about them and keep them to yourself. Share these objectives with your team, get feedback and ask everyone – “Why are we doing this?” Incorporate your teams’ input to the objectives and get them to buy-in to the process.

Customer Journey

Nothing can be more beneficial to your company more than understanding how your customer interacts and experiences your services. There is no greater impact to the success (or failure) of implementing technology than how it will impact the customer experience. Knowing when customer service opportunities and gaps exist in the current mode of operation should have a big impact on where spend your time and money.

On a side note, diagraming the interactions of your customers across all channels should be a must-do regardless of the technology implications.

Business Process Documents/Diagrams

Knowing how the work happens in your business is vital to the impact technology will have – good and bad. Documenting the process & information flows and the interactions between departments narrows your options. Just as important is cataloging the technology currently is place and how its being used. This exercise will help identify duplicate steps, islands of data and opportunities for improvement. If you don’t have this documentation readily available (or is out of date), get on it!

Evaluation Criteria

So you want to sign up for that free trial?! I mean why not, with the fancy video and all those great features, it just has to help my business – right? I’ll say it now – you should absolutely give that a test drive! Just one thing first. What do you need it to do and how are you going to evaluate it?

Ensure you at least have a short list of functions you need from the software and understand how it will support your business. Take your list of criteria and lay it beside the objectives you wrote down. Now draw lines between the criteria and objectives.

Perfect – give that new software a try but keep your evaluation criteria close.


So you have a good handle on why you’re going down the digital path and what you need. You’ve just increased the chance of success significantly. You’re also well  ahead of your competition.

Hopefully throughout this exercise you’ve brought others in to the mix through conversation and discovery. Unless you’re running a solo business, your staff may be the biggest influence on the overall success of your digital business strategy. Engaging other leaders and staff in the business will not only help you get a more complete picture of how the business operates, it gets people engaged in the process. When they are engaged, the chance of adoption and success skyrockets!

You’ll notice that all 5 of these digital business strategy checklist items have nothing to do with new technology.

Starting with the business needs and goals first will help you make informed decisions. If you’re curious to know where this all fits in the master plan, head on over and fill in the blanks.